Skip to main content

Holiday Rentals in Simonʼs Town

Find the holiday rentals that appeal to you the most

Holiday Rentals for every style

Find the right holiday rental for you in Simonʼs Town

The best holiday rentals in Simonʼs Town

Check out our pick of great holiday rentals in Simonʼs Town

Most booked holiday rentals in Simonʼs Town and surroundings in the past month

See all

Popular with guests booking holiday rentals in Simonʼs Town

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 252 reviews

Popular with guests booking holiday rentals in Simonʼs Town

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 169 reviews

Popular with guests booking holiday rentals in Simonʼs Town

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 390 reviews

Popular with guests booking holiday rentals in Simonʼs Town

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 295 reviews

Popular with guests booking holiday rentals in Simonʼs Town

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 198 reviews

Popular with guests booking holiday rentals in Simonʼs Town

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 219 reviews

Popular with guests booking holiday rentals in Simonʼs Town

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 167 reviews

Popular with guests booking holiday rentals in Simonʼs Town

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 520 reviews

Popular with guests booking holiday rentals in Simonʼs Town

Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 739 reviews

Popular with guests booking holiday rentals in Simonʼs Town

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 1,303 reviews

Highly rated holiday rentals in Simonʼs Town and nearby

Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 739 reviews

Featuring a terrace, The Willets Boutique Hotel in Simon's Town is located in Simonʼs Town in the Western Cape region, 1.1 km from Long Beach and 17 km from Chapman's Peak.

From US$96.85 per night
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 78 reviews

Boasting mountain views, Central Hotel Guest House offers accommodation with terrace, around 1 km from Long Beach. With garden views, this accommodation provides a patio.

From US$85.57 per night
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 304 reviews

Offering city views, Ollava Guesthouse is an accommodation situated in Simonʼs Town, 400 metres from Shelly Beach and 14 km from Chapman's Peak.

From US$70.14 per night

Glencairn Haven

Cape Town
8.0+ review score
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 65 reviews

Offering garden views, Glencairn Haven is an accommodation set in Cape Town, 14 km from Chapman's Peak and 28 km from Kirstenbosch National Botanical Garden.

From US$63.13 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 340 reviews

Featuring sea views, 55 on Main Guesthouse and Spa provides accommodation with a terrace, barbecue facilities and a shared lounge, around less than 1 km from Fish Hoek Beach.

From US$95.16 per night

Dunvegan Lodge

Clovelly
8.0+ review score
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 107 reviews

Featuring pool with a view and views of pool, Dunvegan Lodge is a recently renovated villa set in Clovelly, 1.2 km from Fish Hoek Beach.

From US$87.67 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 380 reviews

Boasting panoramic views of Kalk Bay's harbour and False Bay, this attractive guest house is spread over 3 buildings and welcomes guests looking to experience genuine South African hospitality not far...

From US$99.36 per night
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 677 reviews

Boasting garden views, Sonnekus Boutique Hotel & Bistro offers accommodation with a garden, a tennis court and a terrace, around 15 km from Chapman's Peak.

From US$234.05 per night

Enjoy breakfast in Simonʼs Town and nearby

Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 561 reviews

Set in Imhoffʼs Gift and only 12 km from Chapman's Peak, Happy Homes - Imhoffs Gift offers accommodation with sea views, free WiFi and free private parking.

From US$41.10 per night
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 75 reviews

Located in Simonʼs Town and only 1.2 km from Long Beach, Bougainvillea House - The Heart of Simonstown provides accommodation with mountain views, free WiFi and free private parking.

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 9 reviews

Featuring garden views, Regatta View - Simon's Town offers accommodation with a patio, around 1.7 km from Long Beach.

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 3 reviews

Located in Cape Town in the Western Cape region, The Captains Penthouse features a balcony. It is set 1.6 km from Seaforth Beach and provides private check-in and check-out.

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 45 reviews

Located in Simonʼs Town in the Western Cape region, Dolphin Cottage features a patio. This beachfront property offers access to a balcony, free private parking and free WiFi.

Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 11 reviews

Offering a garden and garden view, Spectacular Sea Views Holiday Home is located in Cape Town, 18 km from Chapman's Peak and 26 km from Cape Point.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 57 reviews

Comprising a garden and barbecue facilities, Eclectic Heritage Paradise Simon's Town is a recently renovated accommodation in Simonʼs Town located close to Long Beach.

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 19 reviews

Located in Cape Town and only 1.9 km from Seaforth Beach, Tranquility in Simon's Town provides accommodation with mountain views, free WiFi and free private parking.

These holiday rentals in Simonʼs Town and nearby have options with free cancellation

Leo's Den

Fish hoek
Free cancellation options available
Scored out of 10, guest rating 7.9
Good - What previous guests thought, 237 reviews

Situated just 1.6 km from Fish Hoek Beach, Leo's Den offers accommodation in Fish hoek with access to an open-air bath, a garden, as well as a shared kitchen.

From US$43.84 per night

Albatross Guest House

Simonʼs Town
Free cancellation options available
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 123 reviews

Boasting magnificent views of historical Simon’s Town, False Bay and the mountains beyond, Albatross Guest House overlooks the naval harbour and False Bay Yacht club. Free WiFi is available on site.

No. 1 Living Waters

Simonʼs Town
Free cancellation options available
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 47 reviews

Set in Simonʼs Town and only 1 km from Seaforth Beach, No. 1 Living Waters offers accommodation with mountain views, free WiFi and free private parking.

On The Square Luxury Apartment

Simonʼs Town
Free cancellation options available

On The Square Luxury Apartment, a property with barbecue facilities, is located in Simonʼs Town, 300 metres from Long Beach, 17 km from Chapman's Peak, as well as 25 km from Cape Point.

Mariner Guesthouse & Villa

Simonʼs Town
Free cancellation options available
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 219 reviews

Mariner Guesthouse & Villa is built on the mountainside above the Simon´s Town harbour and offers stunning views across False Bay.

Harbour Views

Simonʼs Town
Free cancellation options available
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 5 reviews

Situated in Simonʼs Town and only 1.5 km from Seaforth Beach, Harbour Views features accommodation with sea views, free WiFi and free private parking.

Admiral's Waterfall Self-Catering

Simonʼs Town
Free cancellation options available
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 37 reviews

Situated in Simonʼs Town and only 1 km from Long Beach, Admiral's Waterfall Self-Catering features accommodation with mountain views, free WiFi and free private parking.

Stonebrook Apartments

Simonʼs Town
Free cancellation options available
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 295 reviews

Featuring mountain views, Stonebrook Apartments features accommodation with balcony, around 1.1 km from Long Beach. With garden views, this accommodation offers a patio.

Holiday Rentals with swimming pools in Simonʼs Town and nearby

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 27 reviews

Located only 300 metres from Seaforth Beach in Simonʼs Town, Penguin Paradise Apartment Simons Town provides accommodation equipped with a patio, garden and year-round outdoor pool.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 20 reviews

Featuring air-conditioned accommodation with a private pool, sea view and a balcony, Penguin Haven. Luxury 2 bedroom, Boulders Beach. Is located in Cape Town.

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 35 reviews

Boasting accommodation with a private pool, sea view and a patio, Restore your Soul, Boulders Beach, Seaforth, Simon's Town is located in Simonʼs Town.

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 49 reviews

Boasting accommodation with a pool with a view, mountain view and a patio, Seaforth Terrace is situated in Simonʼs Town.

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 6 reviews

Set in Cape Town, Neptunes Seat - Garden Paradise with Ocean Views offers accommodation with private pool, free WiFi and free private parking for guests who drive.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 252 reviews

Penguins View Guesthouse has well-equipped self-catering accommodation featuring free WiFi in Simon’s Town, a 5-minute walk from Boulders Beach. Free private parking is available on site.

Whale Rock

Cape Town
Swimming pool
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 120 reviews

Boasting a garden, private pool and pool views, Whale Rock is situated in Cape Town. This beachfront property offers access to a patio, free private parking and free WiFi.

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 53 reviews

Offering a garden and garden view, Blue Mountain Bay is situated in Simonʼs Town, 1.2 km from Fishermans Beach and 22 km from Cape Point.

FAQ about holiday rentals in Simonʼs Town

Holiday rentals that guests love in Simonʼs Town

See all
Avg. price/night: US$96.85
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 739 reviews
Lovely little 3 star hotel in a village! Great bed, top class linen and good coffee/tea offering. It’s an old building so very noisy and try not book a king road facing room!
Guest review by
Karen
Solo traveller
Avg. price/night: US$268.28
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 144 reviews
Central to Boulders beach, very comfortable villa. Kirsty and her staff were excellent.
Guest review by
De Villiers
Young couple
Avg. price/night: US$172.43
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 250 reviews
William, his crew and the lovely Villa is outstanding!
Guest review by
Marc
Solo traveller
Avg. price/night: US$96.85
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 739 reviews
Stunning villa building with friendly staff, centrally located and good breakfast, indoor or out. Thanks!
Guest review by
Adrian
Young couple
Avg. price/night: US$268.28
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 144 reviews
Superb location and the villa itself was amazing, with a private walkway down to the penguin beach.
Guest review by
Alex
Young couple
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 123 reviews
Fantastic views and protected from the wind. You can walk to the village using the steps and footpaths. Welcoming hosts and lovely spacious apartment. We loved our stay.
Guest review by
Lindy
Young couple